Triethylamine → HCID 67193759, compound

HRID 551268Notes

Reaction equation

HRID 551268 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2C(O)=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.CN([C:28]([O:32]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:47]1[CH2:52][CH:51]=[C:50]([C:53]2[CH:54]=[C:55]([CH:58]=[CH:59][CH:60]=2)[C:56]#[N:57])[CH2:49][CH2:48]1>CN(C=O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:14][C:15]([C:28]([N:47]3[CH2:48][CH:49]=[C:50]([C:53]4[CH:54]=[C:55]([CH:58]=[CH:59][CH:60]=4)[C:56]#[N:57])[CH2:51][CH2:52]3)=[O:32])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3577773HCID 3577773, compoundHCID 67194524HCID 67194524, compound

Product 1

HCID 67193759HCID 67193759, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

6-Methoxypyridin-3-ylbenzoic acid (0.7 g, 2.6 mmol) is treated with triethyl amine (0.7 ml, 5 mmol) and TBTU (0.95 g, 3.0 mmol) in DMF (5 ml). 3-(1,2,3,6-Tetrahydropyridin-4-yl)benzonitrile (0.9 g), prepared as above, is added to this suspension and the reaction mixture is heated to 35° C. with stirring for 1.5 h. Solvent is removed, the residue is dissolved in ethyl acetate, and the solution is washed with 1N HCl (2×5 ml). The precipitated solid, 3-{1-[4-(6-methoxypyridin-3-yl)-benzoyl]-1,2,3,6-tetrahydropyridin-4 yl}benzonitrile, is collected (0.60 g); a second crop (0.15 g) is obtained by saturating the organic layer with HCl. 1H NMR (DMSO) δ 8.53 (s, 1H), 8.10 (d, 1H), 7.90 (s, 1H), 7.75 (m, 4H), 4.30 (m, 3H), 6.95 (d, 1H), 6.3 (br, 1H), 4.2 (br, 2H), 3.87 (s, 3H), 3.5 (br, 2H), 2.6 (br, 2H). Ion spray MS M++1: 396.

Workup

  1. additionis added to this suspension
  2. customSolvent is removed
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washthe solution is washed with 1N HCl (2×5 ml)
  5. customThe precipitated solid, 3-{1-[4-(6-methoxypyridin-3-yl)-benzoyl]-1,2,3,6-tetrahydropyridin-4 yl}benzonitrile, is collected (0.60 g)
  6. customa second crop (0.15 g) is obtained
  7. concentrationby saturating the organic layer with HCl

Sources & evidence

ORD record
ord-34044ed31781493fbd89e37a27addc1b
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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